Dihydrostreptomycin

Dihydrostreptomycin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO);
Identifiers
	IUPAC name 2-(2R,3R,4R,5S)-3-(2S,3S,4S,5R,6S)- 4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yloxy-4-hydroxy-4-(hydroxymethyl)- 5-methyloxolan-2-yloxy-3,4,6-trihydroxycyclohexylguanidine;
CAS Number	128-46-1;
PubChem CID	439369;
ChemSpider	388489;
UNII	P2I6R8W6UA;
ChEMBL	ChEMBL1950576;
CompTox Dashboard (EPA)	DTXSID0022937 ;
ECHA InfoCard	100.004.445
Chemical and physical data
Formula	C21H41N7O12
Molar mass	583.596 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC@H1C@@(C@H(C@@H(O1)OC@@H2C@H(C@@H(C@H(C@@H(C@H2O)O)NC(=N)N)O)NC(=N)N)OC@H3C@H(C@@H(C@H(C@@H(O3)CO)O)O)NC)(CO)O;
	InChI InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1; Key:ASXBYYWOLISCLQ-HZYVHMACSA-N;
	(verify)

Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal properties.^[1] It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.^[2]

It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the mRNA and the bacterial ribosome. This leads to the synthesis of defective, nonfunctional proteins, which results in the bacterial cell's death.^[1]

It causes ototoxicity,^[3] which is why it is no longer used in humans.^{[citation needed]}

Referencesedit

^ ^a ^b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
^ Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–3. PMC 3803976. PMID 13186082.

External linksedit

Dihydrostreptomycin | C21H41N7O12 - PubChem

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[ncit-1] "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.

[mesh-2] "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.

[3] Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–3. PMC 3803976. PMID 13186082.

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